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A Phosphorus Analogue of Acenaphthylene

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A 1-phosphaacenaphthylene has been obtained by the deprotonation and collapse of the phosphorus bridge of an appropriate 7-phosphanorbornenium salt. DFT computations showed that the molecule has an elongated P=C double… Click to show full abstract

A 1-phosphaacenaphthylene has been obtained by the deprotonation and collapse of the phosphorus bridge of an appropriate 7-phosphanorbornenium salt. DFT computations showed that the molecule has an elongated P=C double bond of 1.736 A with a strained C–P=C angle of 88.9°. The P lone pair corresponds to the HOMO–2. Its complexation by [W(CO)5] or AuCl induced a clean addition of methanol and water to the P=C double bond. The water addition product was characterized by X-ray crystal structure analysis.

Keywords: phosphorus analogue; analogue acenaphthylene; chemistry; phosphorus

Journal Title: European Journal of Organic Chemistry
Year Published: 2017

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